| Identification | More | [Name]
(S)-(+)-Glycidyl nosylate | [CAS]
115314-14-2 | [Synonyms]
(2S)-(+)-GLYCIDYL-3-NITROBENZENESULFONATE
(2S)-(+)-GLYDICYL-3-NITROBENZENESULFONATE
3-NITROBENZENESULFONIC ACID (S)-GLYCIDYL ESTER
BENZENESULFONIC ACID, 3-NITRO-, (2S)-OXIRANYLMETHYL ESTER
(S)-2,3-EPOXY-1-PROPYL-3-NITROBENZENESULFONATE
(S)-(+)-GLYCIDYL 3-NITROBENZENESULFONATE
(S)-GLYCIDYL 3-NITROBENZENESULFONATE
(S)-(+)-GLYCIDYL-3-NOSYLATE
(S)-(+)-GLYCIDYL NOSYLATE
(S)-GLYCIDYL NOSYLATE
(S)-(+)-OXIRANE-2-METHANOL 3-NITROBENZENESULFONATE
3-nitro-,oxiranylmethylester,(s)-benzenesulfonicaci
oxiranylmethyl(s)-3-nitrobenzenesulfonate
(2S)-(+)-GLYCIDYL 3-NITROBENZENESULFONA
S(+)-GLYCIDYL 3-NITROBENZENELSULFONATE
3-NITRO-BENZENESULFONIC ACID (S)-1-OXIRANYLMETHYL ESTER
(S)-Glycidol 3-Nitrobenzenesulfonate
3-Nitro-benzenesulfonic Acid Oxiranylmethyl Ester
S-Glycidyl-3-Nitrobenzenesulfo
glycidyl 3-nitrobenzenesulfonate | [EINECS(EC#)]
621-475-6 | [Molecular Formula]
C9H9NO6S | [MDL Number]
MFCD00064582 | [Molecular Weight]
259.24 | [MOL File]
115314-14-2.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powde | [Melting point ]
61-65 °C
| [alpha ]
21.5 º (c=2, CHCl3) | [Boiling point ]
432.2±20.0 °C(Predicted) | [density ]
1.5881 (rough estimate) | [refractive index ]
1.5270 (estimate) | [storage temp. ]
-20°C | [solubility ]
Soluble in chloroform, methylene chloride and tetrahydrofuran. Insoluble in hexane. | [form ]
Needles or Powder | [color ]
Off-white to yellow-brown | [Sensitive ]
Moisture Sensitive | [InChI]
InChI=1S/C9H9NO6S/c11-10(12)7-2-1-3-9(4-7)17(13,14)16-6-8-5-15-8/h1-4,8H,5-6H2/t8-/m0/s1 | [InChIKey]
AIHIHVZYAAMDPM-QMMMGPOBSA-N | [SMILES]
C1(S(OC[C@@H]2CO2)(=O)=O)=CC=CC([N+]([O-])=O)=C1 | [CAS DataBase Reference]
115314-14-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R5:Heating may cause an explosion. | [Safety Statements ]
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [RIDADR ]
UN 1325 4.1/PG II | [RTECS ]
DB7192010 | [HazardClass ]
4.1 | [PackingGroup ]
II | [HS Code ]
29209090 |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow crystal powde | [Synthesis]
General procedure for the synthesis of (S)-(+)-m-nitrobenzenesulfonic acid glycidyl ester from 3-nitrobenzenesulfonyl chloride and (R)-oxirane-2-methanol: at -20 °C, m-nitrobenzenesulfonyl chloride (12.6 g, 57 mmol) was slowly added to a solution containing (R)-(+)-glycidol (5.5 g, 74 mmol) and triethylamine (TEA, 10.3 mL. 74 mmol) in a cold solution. The reaction mixture was stirred continuously at -20 °C for 96 hours. Upon completion of the reaction, the reaction solution was filtered and the filtrate was washed sequentially with 10% (w/w) aqueous tartaric acid, saturated saline and deionized water. The washed organic phase was concentrated to afford the target product (S)-(+)-m-nitrobenzenesulfonic acid glycidyl ester in 97% yield. The structure of the product was confirmed by 1H NMR (CDCl3): δ 2.62 (dd, 1H), 2.84 (dd, 1H), 3.22 (m, 1H), 4.07 (dd, 1H), 4.49 (dd, 1H), 7.80 (t, 1H), 8.25 (m, 1H), 8.52 (m, 1H), 8.78 (m, 1H). | [References]
[1] Angewandte Chemie - International Edition, 2013, vol. 52, # 20, p. 5305 - 5308
[2] Angew. Chem., 2013, vol. 125, # 20, p. 5413 - 5416,4
[3] European Journal of Organic Chemistry, 2014, vol. 2014, # 19, p. 4053 - 4069
[4] Patent: US2004/229900, 2004, A1. Location in patent: Page 14
[5] Organic and Biomolecular Chemistry, 2006, vol. 4, # 16, p. 3067 - 3076 |
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